4-Nitrobenzyl chloride → 4-(Pyrrolidin-1-ylmethyl)aniline

Participants

Reaction Steps

Using the procedure of Example 1, 3-ethynyl-phenylamine Compound 54a was used in place of 3-chloro-4-fluoro-phenylamine Compound 1e to prepare 4-chloro-6-(3-ethynyl-phenylamino)-pyrimidine-5-carbonitrile Compound 54b. MS 255 (MH+). Using the procedure of Example 1, Compound 54b was used in place of Compound 1f to prepare 5-(3-ethynyl-phenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,6,8-tetraaza-acenaphthylene-2-carboxylic acid Compound 54c. MS 335 (M−). Using the procedure of Example 1, pyrrolidine was used in place of piperidine and combined with 1-chloromethyl-4-nitro-benzene Compound 1i and taken forward to provide 4-pyrrolidin-1-ylmethyl-phenylamine Compound 54e. MS 177 (MH+). Using the procedure of Example 2, Compound 54c was used in place of Compound 40 and Compound 54e was used in place of 3,4-dimethoxy-phenylamine Compound 2c to give Compound 15. MS 495 (MH+).

Provenance & Evidence